| 1. Round | 16/09/1998 | Chelsea FC | - | Helsingborgs IF | 1:0 | ||||
| 1. Round | 30/09/1998 | Helsingborgs IF | - | Chelsea FC | 0:0 | ||||
| 2. Round | 21/10/1998 | Chelsea FC | - | FC København | 1:1 | ||||
| 2. Round | 04/11/1998 | FC København | - | Chelsea FC | 0:1 | ||||
| Quarter-finals | 03/03/1999 | Chelsea FC | - | Vålerenga IF | 3:0 | ||||
| Semi-finals | 08/04/1999 | Chelsea FC | - | RCD Mallorca | 1:1 | ||||
| Semi-finals | 22/04/1999 | RCD Mallorca | - | Chelsea FC | 1:0 |
Spain